Related Experiment Video
Updated: Dec 18, 2025

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Gas Phase Identification of the Elusive N-Hydroxyoxaziridine (c-H2CON(OH)): A Chiral Molecule
Santosh K Singh1,2, Tang-Yu Tsai3, Bing-Jian Sun3
1Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
Abstract:
The hitherto elusive N-hydroxyoxaziridine molecule (c-H2CON(OH)), a chiral, high energy isomer of nitromethane (CH3NO2) and one of the simplest representatives of an oxaziridine, is detected in the gas phase. Electronic structure calculations propose an impending synthesis eventually via addition of carbene (CH2) to the nitrogen-oxygen double bond of nitrous acid (HONO). The oxaziridine ring demonstrates an unusual kinetic stability toward ring opening compared to the isoeletronic cyclopropane (C3H6) counterpart. This system defines a fundamental benchmark to explore the formation and stability of racemic derivatives of strained oxaziridines (c-H2CONH) and changes our perception how we think about fundamental decomposition and isomerization mechanisms in (model compounds of) energetic materials.
Related Concept Videos
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Prochirality
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Mass Spectrum: Interpretation
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
